Crafting a Data-Driven Upsell Strategy
In 2023, I was the lead designer for Trainline’s “Inbound” market—an internal label for travelers from outside Europe. Although we sold tickets worldwide, we’d never tailored any product experience to this high-value segment.
Our team’s goal was clear: increase net ticket sales among Inbound users by introducing a first-class upsell. Through user interviews and booking behavior data analysis, we uncovered three powerful insights.
Target Audience: US Inbound
Seasonal Booking Patterns
Inbound travelers book further in advance and
take fewer, longer trips than our domestic base
Luxury Expectations
They imagine European rail as a luxury, story-book experience
High-Value Travelers
Their average transaction value exceeds that of our typical customers
Armed with these learnings, we built a class-upsell system—starting with a simple modal and evolving over several months into an AI-powered, personalized experience—that delivered sustained uplift in first-class adoption.
First Iteration:
Targeted Modal
We rolled out a simple pop-up each time an Inbound user picked a standard fare, quickly validating interest in first-class. Given their infrequent, far-in-advance booking habits, a lightweight, contextual prompt was the ideal first UX step.
As Inbound travelers had limited awareness of first class, our copy had to bridge that gap—feeling familiar enough to build trust, yet exciting enough to inspire an upgrade.
Despite being a lightweight addition, the feature significantly improved how Inbound users discovered and booked first-class tickets.
+23% in 1st class tickets sold
+8% CvR
Rich Visuals,
Modern UI,
Smart Global Context
Building on our initial wins, we set out to roll the upsell experience across our global user base. Research showed that immersive imagery drove engagement, so we partnered with train operators to capture high-quality photos of first-class cabins.
We modernized the UI—updating typography, spacing, and color accents for a premium feel—and reworked the display of services logic to only surface the services that were key in decision making.
Real cabin photos
-> Modern UI
Refined type, spacing & clearer service cards
-> Data-powered
service ordering
We organized all services into categories (Seats, Meals, Wi-Fi, etc.) and defined a priority ranking within each group.
When generating the upsell card, our logic picks the top-ranked option from each category (which differs between carriers), so users see the most relevant services without clutter.
Identify High-Value
Segments
Knowing that our customers were engaging with the upsell modal, we wanted to find which user groups were more receptive to a bolder approach.
We ran an EU-wide pre-selection test, making first class the chosen option at the top of the fare list, and then measured both uptake and overall conversion across dozens of user attributes.
Analysis enabled us to identify user groups (based on some of those attributes) for which 1st class uptake was high, and conversion flat, in order to apply the pre-selection experience only to those groups.
We then layered-in dynamic copy and visuals for each segment, and achieved massive uptake. This paved the way for our ML model.
-> …with predictive insights
With everything we learned, we built a ML Model (some of it is running on Apple's foundation models) allowing us to target the right customer, at the right time, with the right upsell experience
Extending the
Premium Experience
To celebrate our first-class travelers and amplify their sense of exclusivity, we layered premium touches beyond the booking flow:
Unlockable App Icons: Exclusive icons awarded post–first-class booking to reinforce premium status.
Custom eTickets: Redesigned with gold accents and device-movement metallic effects for a memorable ticket scan.
These small moments of delight not only helped exceed our targets but also influenced our retention rates as upgrade feel genuinely special.
Internal Marketing: Release Videos
At Trainline, I turned every feature launch—and even our A/B test updates—into a brief, engaging motion-design video. These internal release films became my go-to way to rally the company around new features and experiences that the team shipped.
Below are the videos I crafted for the class-upsell project: